A Soluble Polyaniline Substituted with t-BOC:  Conducting Patterns and Doping

Abstract

A soluble polyaniline (PANi) was synthesized by modifying with a photolabile, acid-labile, and thermolabile tert-butoxycarbonyl (t-BOC) group in this study. The prepared PANi(t-BOC) is highly soluble and thermodynamically stable in low-boiling solvents such as THF, dioxane, and CHCl 3. This soluble form of PANi(t-BOC) was converted to the insoluble and electrically conductive emeraldine salts upon photodoping with only a catalytic amount of photoacid generators such as N-(tosyloxy)-or (camphorsulfonyloxy)norborneneimide or -onium salts. As a result of this solubility difference, conducting patterns of high resolution were produced by conventional photolithography process. Further, upon removal of the t-BOC groups in PANi(t-BOC) by acid doping, no obvious morphology change of the films was observed, and such conversion recovered the original conductivity level of the doped PANi. Since the t-BOC protecting groups are easily removed in doping or acid-catalyzed reaction by chemical amplification or thermal bake, the PANi(t-BOC) can be used as conductive matrix polymers for negative type photoimaging or printing materials or for novel solution-processed applications in various microelectronic devices.

High-Performance Polyaniline Prepared via Polymerization in a Self-Stabilized Dispersion

“…It is interesting to note also that these NMR peaks, particularly the peaks observed around 137 ppm, are consistent with the idealized repeat structure of EB because two resonances are expected from the protonated carbons C4 in the quinoid ring owing to the absence of rotation on the bent linkage of imine group N±. [17,18] …”

Size‐Controlled Fabrication of Polyaniline Microfibers Based on 3D Hydrodynamic Focusing Approach

“…The PANI and t -Boc-protected PANI were prepared according to the method reported in the literature. [ 29,30 ] The strong sulfonic acid would remove the t -Boc protecting group and forms the DBSA-doped PANI. A microfl uidic chip capable of 3D hydrodynamic focusing was employed for the fabrication of PANI microfi bers ( Figure 2 ).…”

“…The decreased conductivity of CSA redoped PANI, prepared from t -Boc-protected PANI, has been previously reported. [ 30 ] In addition, the absence of m -cresol, which serves as a secondary dopant, might also contribute to the decreased conductivity.…”

Organic Chemistry of Polyanilines: Tailoring Properties to Technological Applications~!2008-08-19~!2008-09-11~!2008-11-28~!

“…A soluble polyaniline was also synthesized by modifying with a photolabile, acid-labile, and thermolabile tert-butoxycarbonyl (t-BOC). The group could be removed afterwards rendering polyaniline, giving the basis of a photolithographic process [42].…”